The main feature of art and architecture of Certaldo Alto, for which it became known and popular in Europe, is the perfectly preserved medieval aspect, with its narrow streets and small squares you find here and there; if we exclude the restructuring work over the Palazzo Pretorio in the fifteenth century (the old tower was transformed in the palace of the vicar), we can say that Certaldo Alto remained identical to what it was in the Middle Ages.

Further evidence of this feature is the lack of a large square in the ancient village centre. Instead of it, we find a long, wide street (Via Boccaccio) which carried out all functions of a square, representing the public place, which was typical of the first medieval Age.